As I’ve tried explaining to my husband time and time again—to no avail, of course—you can truly never have enough pairs of black boots. This is especially true for myself, who lives almost exclusively in the shoe style (in one form or another) for most of fall and winter. It’s also true for any girl living in NYC, really, where the name of the game is functionality. You need your casual boots, your heeled boots, your snow boots, and everything in between. Then if you’re a stickler for details like me, you’ll find that there are subcategories within all of these categories that must be fulfilled as well. For example, the casual boot that won’t get ruined in the rain, the plain pair, and the statement style. Or the heeled boot that looks good with trousers, one for long jeans, one for short jeans, one for dresses and skirts, etc. I could go on and on, but instead, I’ll cut to the chase.

Despite owning more pairs of black boots than anyone should ever admit to in multiple closets and storage situations across America, I’ll always be compelled to buy more of my favorite shoe category—but only if they’re good enough. With that in mind, I figured I’d round up the styles I’m eyeing at the moment, plus share with you some pairs I’m already wearing on the regular. Naturally, that total came out to 26 pairs. To get started (and shopping), just keep scrolling. 

The ones you clicked into this story for.

These look way more expensive than their price tag.

Chunky boots are my go-to for walking around the city.

This is my ideal heel height for a nighttime boot.

So sleek.

These will add a cool edge to every outfit.

The boot silhouette all the cool girls are wearing right now.

Perfect for a day in the great outdoors.

These sleek rainboots won’t dampen your style.

I got so many compliments on these recently that I had to share.

A classic pair of Chelsea boots will last you a lifetime.

I love the zip detail.

Pair with tights and a floral midi dress.

A taller bootie exudes a modern touch.

Keep your toes toasty in this puffer boot that’s temperature rated to -32º.

These will take you from day-to-night in style.

Slip these on under all your winter dresses.

Always the goal.

Did I just find the perfect winter boot?

I adore a chic black suede bootie.

Simply perfect.

Made from buttery leather these will add sophistication to your look.

A square-toe feels fresh and current.

Loving the cozy textures here.

Love them or hate them, they’ll certainly keep you cozy.

Comfy for commuting.

This post was published at an earlier date and has since been updated.

Up next, The “Weird” Micro-Trend I’m Betting Big on This Fall